(4S)-4beta-[(S)-1,2,3,4-Tetrahydro-6-methoxy-7-hydroxyisoquinoline-1-ylmethyl]-5beta-vinyl-6alpha-(beta-D-glucopyranosyloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid

Details

• Internal ID: 2669156b-bd68-41ef-8b11-708755f26757
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S)-3-ethenyl-4-[[(1S)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
• SMILES (Canonical): COC1=C(C=C2C(NCCC2=C1)CC3C(C(OC=C3C(=O)O)OC4C(C(C(C(O4)CO)O)O)O)C=C)O
• SMILES (Isomeric): COC1=C(C=C2[C@@H](NCCC2=C1)C[C@H]3[C@H]([C@@H](OC=C3C(=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C=C)O
• InChI: InChI=1S/C25H33NO11/c1-3-12-14(7-16-13-8-17(28)18(34-2)6-11(13)4-5-26-16)15(23(32)33)10-35-24(12)37-25-22(31)21(30)20(29)19(9-27)36-25/h3,6,8,10,12,14,16,19-22,24-31H,1,4-5,7,9H2,2H3,(H,32,33)/t12-,14+,16+,19-,20-,21+,22-,24+,25+/m1/s1
• InChI Key: SQIULMODQKFOOJ-ONGZBVEHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₃NO₁₁
• Molecular Weight: 523.50 g/mol
• Exact Mass: 523.20536087 g/mol
• Topological Polar Surface Area (TPSA): 187.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -0.46
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7848	78.48%
Caco-2	-	0.9070	90.70%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Nucleus	0.5106	51.06%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.7877	78.77%
OATP1B3 inhibitior	+	0.9440	94.40%
MATE1 inhibitior	-	0.9220	92.20%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7287	72.87%
P-glycoprotein inhibitior	-	0.5935	59.35%
P-glycoprotein substrate	+	0.5486	54.86%
CYP3A4 substrate	+	0.6737	67.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8261	82.61%
CYP3A4 inhibition	-	0.9125	91.25%
CYP2C9 inhibition	-	0.8644	86.44%
CYP2C19 inhibition	-	0.8087	80.87%
CYP2D6 inhibition	-	0.6484	64.84%
CYP1A2 inhibition	-	0.6617	66.17%
CYP2C8 inhibition	+	0.6363	63.63%
CYP inhibitory promiscuity	-	0.9156	91.56%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6704	67.04%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9434	94.34%
Skin irritation	-	0.7545	75.45%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.5293	52.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.7860	78.60%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.6193	61.93%
skin sensitisation	-	0.7950	79.50%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7702	77.02%
Acute Oral Toxicity (c)	III	0.6495	64.95%
Estrogen receptor binding	+	0.8092	80.92%
Androgen receptor binding	+	0.5754	57.54%
Thyroid receptor binding	+	0.5844	58.44%
Glucocorticoid receptor binding	+	0.6343	63.43%
Aromatase binding	+	0.6033	60.33%
PPAR gamma	+	0.6302	63.02%
Honey bee toxicity	-	0.7208	72.08%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.3616	36.16%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.71%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.52%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.05%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.92%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.58%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.17%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.04%	89.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.17%	82.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.79%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.39%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.13%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.70%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.45%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.56%	90.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.30%	89.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.85%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.41%	95.89%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.00%	95.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 637480
• LOTUS: LTS0098519
• wikiData: Q105257963